12-Hydroxy-3-dodecenoic acid | 73961-79-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 12-Hydroxy-3-dodecenoic acid
• 英文别名: 12-hydroxydodec-3-enoic acid
• CAS: 73961-79-2
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: RRJILZUCEDMMNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-Hydroxy-3-dodecenoic acid 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 以88%的产率得到(Z)-dodec-3-en-12-olide
  参考文献：
  名称：

  Concise Synthesis of (3Z)-Dodecen-12-olide, Pheromone Component of the Emerald Ash Borer

  摘要：

  Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is an invasive insect that has killed millions of ash trees in Canada and the USA. (3Z)-Dodecen-12-olide is a known female-produced pheromone of this insect, and a concise, three-step synthesis of a 2:1 blend of (3Z)-dodecen-12-olide and (3E)-dodecen-12-olide starting from commercially available (2-carboxyethyl)triphenylphosphonium bromide and 10-bromo-1-decene is described. The key steps in this synthesis are a lithium-salt-free Wittig reaction and an intramolecular S(N)2 esterification. Both of these macrocyclic lactones are behaviorally active toward EAB, and the 2:1 blend whose synthesis is described here has the potential to be a detection agent, mating disruptor, or mass trapping agent, which could be used in the control of EAB.

  DOI：

  10.1080/00397911.2014.881497
• 作为产物：
  描述：

  tert-butyl(dec-9-en-1-yloxy)dimethylsilane 在 sodium chlorite 、 3-甲基-1-环己烯 、 氨基磺酸 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 对甲苯磺酸 、 臭氧 、 苏丹红 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 12-Hydroxy-3-dodecenoic acid
  参考文献：
  名称：

  Concise Synthesis of (3Z)-Dodecen-12-olide, Pheromone Component of the Emerald Ash Borer

  摘要：

  Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is an invasive insect that has killed millions of ash trees in Canada and the USA. (3Z)-Dodecen-12-olide is a known female-produced pheromone of this insect, and a concise, three-step synthesis of a 2:1 blend of (3Z)-dodecen-12-olide and (3E)-dodecen-12-olide starting from commercially available (2-carboxyethyl)triphenylphosphonium bromide and 10-bromo-1-decene is described. The key steps in this synthesis are a lithium-salt-free Wittig reaction and an intramolecular S(N)2 esterification. Both of these macrocyclic lactones are behaviorally active toward EAB, and the 2:1 blend whose synthesis is described here has the potential to be a detection agent, mating disruptor, or mass trapping agent, which could be used in the control of EAB.

  DOI：

  10.1080/00397911.2014.881497

文献信息

• Enecarboxylation with diethyl oxomalonate as an enophilic equivalent of carbon dioxide. A synthesis of allylcarboxylic acids
  作者：Mary F. Salomon、Simon N. Pardo、Robert G. Salomon

  DOI：10.1021/ja00325a014

  日期：1984.6

  On prepare une serie d'acides carboxyliques allyliques a partir des olefines correspondantes par un processus en deux etapes equivalent a: 1) une reaction ene avec l'oxomalonate de diethyle conduisant a l'ester α-hydroxymalonique; 2) une bisdecarboxylation oxydante de ce dernier

  在制备 une serie d'acides carboxyliques allyliques a partir des ocoxyliques par un processus en deux etapes 等价物 a: 1) une 反应 ene avec l'oxomalonate de diethyle conduisant a l'ester α-hydroxymalonique; 2) une bisdecarboxylation oxydante de ce dernier